This invention relates to artificial sweetener compounds and compositions and to a process for preparing same. The novel sweetener compound, 3-(m-hydroxyphenyl)phloropropiophenone, is disclosed.
Hesperetin dihydrochalcone, and alkyl homologs thereof, have been previously suggested for use as artificial sweeteners; see the copending applications of Rizzi, entitled "Dihydrochalcone Sweetening Agent", Ser. No. 76,972, filed Sept. 30, 1970; "Improved Sugar Compositions", Ser. No. 76,974, filed Sept. 30, 1970; and Rizzi and Neely, "Sweetening Compositions", Ser. No. 76,973, filed Sept. 30, 1970.
Heretofore, the preparation of arylphloropropiophenone sweeteners, such as hesperetin dihydrochalcone and its alkyl homologs, has been carried out by using various naturally-occurring precursor materials such as homoneohesperetin and various flavonone glycosides (see the foregoing references). Such naturally-occurring precursor materials are known to be expensive and available only in limited quantities. Furthermore, the use of naturally-occurring precursor materials does not provide a method for synthesizing useful 3-arylphloropropiophenones not found in nature, e.g., the novel artificial sweetener compound, 3-(m-hydroxyphenyl)phloropropiophenone, disclosed herein. For these reasons, it is desirable to provide a process for preparing 3-arylphloropropiophenones, such as hesperetin dihydrochalcone and analogs thereof, which does not require the use of naturally-occurring precursor materials.
Zemplin and Bognar, Chem. Ber., 75, 1043 (1942) disclose a method for preparing hesperetin dihydrochalcone using glycoside intermediates. While this procedure does yield the desired hesperetin dihydrochalcone reaction products, it is far too complex for use on an industrial scale.
It is an object of this invention to provide a novel 3-arylphloropropiophenone compound, 3-(m-hydroxyphenyl)phloropropiophenone, and sweetener compositions containing same. It is a further object herein to provide a process for preparing 3-arylphloropropiophenones, such as hesperetin dihydrochalcone, and certain analogs and homologs thereof, which does not require the use of naturally-occurring precursor materials. These and other objects are obtained by this invention as will be seen from the following disclosure.